4
/24:
The Late 90s

4/24
:The Late 90s

5
/24:
The early 2000s

5/24
:The early 2000s

Share

Tweet

Pin

By now, Gwen was a bit more established in her career and she was still changing up her look all the time. Hats were definitely a fave for the singer at this point, and so was the urban look. Cargo pants, funky tops and the like reigned supreme in her street and red carpet looks.

8/24
:The Early 2000s

9
/24:
The Mid 2000s

9/24
:The Mid 2000s

Share

Tweet

Pin

As Gwen embarked on a solo career, launched her own clothing line and settled into married life, she again switched up her look a bit. We started to see a classy side of Gwen on the red carpet but her inner sporty, urban chick still came out quite often.